5-bromo-4-chloro-2-ethyl-1H-benzimidazole → 4-chloro-2-ethyl-1H-benzimidazole-5-carbonitrile

HRID 913569Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 913569
Br[C:2]1[CH:12]=[CH:11][C:5]2[NH:6][C:7]([CH2:9][CH3:10])=[N:8][C:4]=2[C:3]=1[Cl:13].[C:14]([Cu])#[N:15]>CN1C(=O)CCC1>[Cl:13][C:3]1[C:4]2[N:8]=[C:7]([CH2:9][CH3:10])[NH:6][C:5]=2[CH:11]=[CH:12][C:2]=1[C:14]#[N:15]

Komponenten

4

Edukt 2

HCID 578001585-bromo-4-chloro-2-ethyl-1H-benzimidazoleHCID 178418546HCID 178418546, Verbindung

Produkt 1

HCID 674049024-chloro-2-ethyl-1H-benzimidazole-5-carbonitrileAusbeute 35,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
220 °C

Versuchsvorschrift

5-Bromo-4-chloro-2-ethyl-1H-benzimidazole (0.050 g, 0.192 mmol) and CuCN (0.030 g, 0.576 mmol) were combined in NMP (3 mL) and heated to 220° C. for 20 min in a microwave. The cooled mixture was partitioned between Et2O and water. The organic portion was washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. Purification (SiO2, EtOAc/hexanes) afforded the title compound (0.014 g): MS (ESI) m/z 206 (M+1).

Aufarbeitung

  1. customThe cooled mixture was partitioned between Et2O and water
  2. washThe organic portion was washed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification (SiO2, EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-726f7b16115b4859b4127be5efff1667
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08026262B2

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